Application of umbelliferone molecularly imprinted polymer in analysis of plant samples
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Katarína Hroboňová
,
Andrea Spevak
Abstract
The molecularly imprinted polymers (MIPs) were synthesised and the influence of the type of porogen, the nature of sample solvent, and the binding capacity of material were tested by high-performance liquid chromatography (HPLC). Umbelliferone was used as the template for imprint formation. Methacrylic acid was used as the monomer and acetonitrile, ethanol, and chloroform as porogen. Non-imprinted polymers (NIPs) were prepared by the same procedure. The highest value of the specific binding capacity (269 μg of umbelliferone per 100 mg of polymer) was obtained for polymers prepared in chloroform as porogen and methanol/water (φ r = 1: 1) as the sample solvent. The group-selective MIP was used as sorbent for the SPE pre-treatment of umbelliferone from plant extracts prior to HPLC analysis. Analysis of the spiked samples showed good recoveries (> 77 %). The limit of detection, limit of determination, and repeatability of the method were also calculated.
[1] Blahová, E., & Brandšteterová, E. (2004). Approaches in sample handling before HPLC analysis of complex matrices. Chemical Papers, 58, 362–373. Search in Google Scholar
[2] Ciésla, Ł., & Waksmundzka-Hajnos, M. (2009). Two-dimensional thin-layer chromatography in the analysis of secondary plant metabolites. Journal of Chromatography A, 1216, 1035–1052. DOI: 10.1016/j.chroma.2008.12.057. http://dx.doi.org/10.1016/j.chroma.2008.12.05710.1016/j.chroma.2008.12.057Search in Google Scholar
[3] Chen, D., Wang, J., Jiang, Y., Zhou, T., Fan, G., & Wu, Y. (2009). Separation and determination of coumarins in Fructus cnidii extracts by pressurized capillary electrochromatography using a packed column with a monolithic outlet frit. Journal of Pharmaceutical and Biomedical Analysis, 50, 695–702. DOI: 10.1016/j.jpba.2009.05.026. http://dx.doi.org/10.1016/j.jpba.2009.05.02610.1016/j.jpba.2009.05.026Search in Google Scholar
[4] Dawa, Z., Zhou, Y., Bai, Y., Gesang, S., Bai, B., & Ding, L. (2008). Development of an HPLC-DAD-ESI-MSn method for quantitative analysis of Saussurea tridactyla. Journal of Pharmaceutical and Biomedical Analysis, 48, 1076–1081. DOI: 10.1016/j.jpba.2008.08.016. http://dx.doi.org/10.1016/j.jpba.2008.08.01610.1016/j.jpba.2008.08.016Search in Google Scholar
[5] Dias, A. C. B., Figueiredo, E. C., Grassi, V., Zagatto, E. A. G., & Arruda, M. A. Z. (2008). Molecularly imprinted polymer as a solid phase extractor in flow analysis. Talanta, 76, 988–996. DOI: 10.1016/j.talanta.2008.05.040. http://dx.doi.org/10.1016/j.talanta.2008.05.04010.1016/j.talanta.2008.05.040Search in Google Scholar
[6] Fernández Izquierdo, M. E., Quesada Granados, J., Villalon Mir, M., & López Martinez, M. C. (2000). Comparison of methods for determining coumarins in distilled beverages. Food Chemistry, 70, 251–258. DOI: 10.1016/s0308-8146(00)00071-6. http://dx.doi.org/10.1016/S0308-8146(00)00071-610.1016/S0308-8146(00)00071-6Search in Google Scholar
[7] Fonseca, F. N., Tavares, M. F. M., & Horváth, C. (2007). Capillary electrochromatography of selected phenolic compounds of Chamomilla recutita. Journal of Chromatography A, 1154, 390–399. DOI: 10.1016/j.chroma.2007.03.106. http://dx.doi.org/10.1016/j.chroma.2007.03.10610.1016/j.chroma.2007.03.106Search in Google Scholar
[8] Haupt, K., Dzgoev, A., & Mosbach, K. (1998). Assay system for the herbicide 2,4-dichlorophenoxyacetic acid using a molecu larly imprinted polymer as an artificial recognition element. Analytical Chemistry, 70, 628–631. DOI: 10.1021/ac9711549. http://dx.doi.org/10.1021/ac971154910.1021/ac9711549Search in Google Scholar
[9] Hoult, J. R. S., & Paya, M. (1996). Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. General Pharmacology, 27, 713–722. DOI: 10.1016/0306-3623(95)02112-4. http://dx.doi.org/10.1016/0306-3623(95)02112-410.1016/0306-3623(95)02112-4Search in Google Scholar
[10] Jurd, L., King, A. D., Jr., & Mihara, K. (1971). Antimicrobial properties of umbelliferone derivatives. Phytochemistry, 10, 2965–2970. DOI: 10.1016/s0031-9422(00)97333-3. http://dx.doi.org/10.1016/S0031-9422(00)97333-310.1016/S0031-9422(00)97333-3Search in Google Scholar
[11] Kaneko, T., Baba, N., & Matsuo, M. (2003). Protection of coumarins against linoleic acid hydroperoxide-induced cytotoxicity. Chemico-Biological Interactions, 142, 239–254. DOI: 10.1016/s0009-2797(02)00077-7. http://dx.doi.org/10.1016/S0009-2797(02)00077-710.1016/S0009-2797(02)00077-7Search in Google Scholar
[12] Lépinay, S., Kham, K., Millot, M. C., & Carbonnier, B. (2012). In-situ polymerized molecularly imprinted polymeric thin films used as sensing layers in surface plasmon resonance sensors: Mini-review focused on 2010–2011. Chemical Papers, 66, 340–351. DOI: 10.2478/s11696-012-0134-6. http://dx.doi.org/10.2478/s11696-012-0134-610.2478/s11696-012-0134-6Search in Google Scholar
[13] Malik, A., Kushnoor, A., Saini, V., Singhal, S., Kumar, S., & Yadav, Y. C. (2012). Analytical methods development of nutraceutical: Umbelliferone. Pharma Science Monitor: An International Journal of Pharmaceutical Sciences, 3, 67–73. Search in Google Scholar
[14] Micke, G. A., Moraes, E. P., Farah, J. P. S., & Tavares, M. F. M. (2003). Assessing the separation of neutral plant secondary metabolites by micellar electrokinetic chromatography. Journal of Chromatography A, 1004, 131–143. DOI: 10.1016/s0021-9673(03)00935-x. http://dx.doi.org/10.1016/S0021-9673(03)00935-X10.1016/S0021-9673(03)00935-XSearch in Google Scholar
[15] Nie, J. F., Wu, H. L., Zhu, S. H., Han, Q. J., Fu, H. Y., Li, S. F., & Yu, R. Q. (2008). Simultaneous determination of 6-methylcoumarin and 7-methoxycoumarin in cosmetics using three-dimensional excitation-emission matrix fluorescence coupled with second-order calibration methods. Talanta, 75, 1260–1269. DOI: 10.1016/j.talanta.2008.01.026. http://dx.doi.org/10.1016/j.talanta.2008.01.02610.1016/j.talanta.2008.01.026Search in Google Scholar
[16] Nováková, L., Vildová, A., Mateus, J. P., Gonçalves, T., & Solich, P. (2010). Development and application of UHPLC-MS/MS method for the determination of phenolic compounds in Camomile flowers and Camomile tea extracts. Talanta, 82, 1271–1280. DOI: 10.1016/j.talanta.2010.06.057. http://dx.doi.org/10.1016/j.talanta.2010.06.05710.1016/j.talanta.2010.06.057Search in Google Scholar
[17] Sgorbini, B., Ruosi, M. R., Cordero, C., Liberto, E., Rubiolo, P., & Bicchi, C. (2010). Quantitative determination of some volatile suspected allergens in cosmetic creams spread on skin by direct contact sorptive tape extraction-gas chromatography-mass spectrometry. Journal of Chromatography A, 1217, 2599–2605. DOI: 10.1016/j.chroma.2009.12. 052. http://dx.doi.org/10.1016/j.chroma.2009.12.05210.1016/j.chroma.2009.12.052Search in Google Scholar
[18] Solich, P., Polášek., M., & Karlíček, R. (1995). Sequential flowinjection spectrofluorimetric determination of coumarins using a double-injection single-line system. Analytica Chimica Acta, 308, 293–298. DOI: 10.1016/0003-2670(94)00660-e. http://dx.doi.org/10.1016/0003-2670(94)00660-E10.1016/0003-2670(94)00660-ESearch in Google Scholar
[19] Su, J., Zhang, C., Zhang, W., Shen, Y. H., Li, H. L, Liu, R. H., Zhang, X., Hu, X. J., & Zhang, W. D. (2009). Qualitative and quantitative determination of the major coumarins in Zushima by high performance liquid chromatography with diode array and mass spectrometry. Journal of Chromatography A, 1216, 2111–2117. DOI: 10.1016/j.chroma.2008.06.015. http://dx.doi.org/10.1016/j.chroma.2008.06.01510.1016/j.chroma.2008.06.015Search in Google Scholar PubMed
[20] Tamayo, F. G., Turiel, E., & Martín-Esteban, A. (2007). Molecularly imprinted polymers for solid-phase extraction and solid-phase microextraction: Recent developments and future trends. Journal of Chromatography A, 1152, 32–40. DOI: 10.1016/j.chroma.2006.08.095. http://dx.doi.org/10.1016/j.chroma.2006.08.09510.1016/j.chroma.2006.08.095Search in Google Scholar PubMed
[21] Wang, W., Tang, J., Wang, S., Zhou, L., & Hu, Z. (2007). Method development for the determination of coumarin compounds by capillary electrophoresis with indirect laserinduced fluorescence detection. Journal of Chromatography A, 1148, 108–114. DOI: 10.1016/j.chroma.2006.09.070. http://dx.doi.org/10.1016/j.chroma.2006.09.07010.1016/j.chroma.2006.09.070Search in Google Scholar PubMed
[22] Zheng, C., Huang, Y. P., & Liu, Z. S. (2011). Rescent developments and applications of molecularly imprinted monolithic column for HPLC and CEC. Journal of Separation Science, 34, 1988–2002. DOI: 10.1002/jssc.201100164. 10.1002/jssc.201100164Search in Google Scholar PubMed
© 2013 Institute of Chemistry, Slovak Academy of Sciences
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Articles in the same Issue
- Application of umbelliferone molecularly imprinted polymer in analysis of plant samples
- Determination of antioxidant activity using oxidative damage to plasmid DNA — pursuit of solvent optimization
- Nanosized sulfated zirconia as solid acid catalyst for the synthesis of 2-substituted benzimidazoles
- Removal of heavy metal ions from aqueous solutions using low-cost sorbents obtained from ash
- Base-catalysed reduction of pyruvic acid in near-critical water
- Solubility and micronisation of phenacetin in supercritical carbon dioxide
- Synthesis of nanostructured perovskite powders via simple carbonate co-precipitation
- Three-component one-pot reaction for the synthesis of β-amide ketones
- Spectral analysis of naringenin deprotonation in aqueous ethanol solutions
- Provenance study of volcanic glass using 266–1064 nm orthogonal double pulse laser induced breakdown spectroscopy
- A new, fully validated and interpreted quantitative structure-activity relationship model of p-aminosalicylic acid derivatives as neuraminidase inhibitors
- Interaction of oligonucleotides with benzo[c]phenanthridine alkaloid sanguilutine
